In an order fulfilment center, automated induction of random items into flexible packaging, such as flexible envelopes, for the shipment and/or delivery of single-item or multi-item orders presents significant challenges. These challenges are compounded in fulfillment centers that process items of varying sizes and shapes. In current automated packaging systems, if the package is preformed, then items often end up in unfavorable or otherwise unorganized orientations, and can even become “stuck” in the package, particularly if numerous items are inducted into the package. This problem is particularly prevalent when items are inducted into the package via gravity, and significant efforts to reposition items in the package are often required. Moreover, for automated flexible packaging systems, any translation of the combined items and internal padding material while moving this combination to a position to create the flexible package around the combination can cause the items to shift, resulting in interference with the formation of the package. Additionally, certain padding materials within the package, such as paper meshes, exhibit diminished cushioning qualities when the constituent components of the mesh or not oriented in a uniform manner.